title: Bromodimethylsulfonium bromide/silver triflate-promoted glycosylations using glycosyl allenoates as donors.
abstract: A series of novel glycosyl allenoates were prepared by condensions of hemiacetals with 3,3-dimethyl-4,5-allenoic acid. Their glycosylations with various alcohols under the promotion of bromodimethylsulfonium bromide/silver triflate smoothly proceeded to produce disaccharides. Studies reveal that allenic group is crucial for the efficient glylcosylation of glycosyl allenoate.
authors.affiliation: Key Laboratory of Marine Medicine, Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao, 266003 Shandong, China.
authors.forename: Yongzhen
authors.initials: Y
authors.lastname: Zhang
authors.forename: Peng
authors.initials: P
authors.lastname: Wang
authors.forename: Ni
authors.initials: N
authors.lastname: Song
authors.forename: Ming
authors.initials: M
authors.lastname: Li
mesh_terms: D000466:Alkadienes / Q000138:chemical synthesis / Q000737:chemistry*; D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis / Q000737:chemistry*; D006031:Glycosylation; D008698:Mesylates / Q000737:chemistry*; D015394:Molecular Structure; D013452:Sulfonium Compounds / Q000737:chemistry*
chemical_list: D000466:Alkadienes; D004187:Disaccharides; D006027:Glycosides; D008698:Mesylates; D013452:Sulfonium Compounds; C012077:trifluoromethanesulfonic acid
keywords: Bromodimethylsulfonium bromide; Glycosyl allenoate; Glycosylation; Silver triflate